The ability of 2-phosphabicyclo[2.2.2]oct-5-ene 2-oxides to undergo fragmentation of the bridging P-moiety

G. Keglevich, Kinga Steinhauser, György Miklós Keseru, Zsolt Böcskei, K. Újszászy, G. Marosi, Imre Ravadits, L. Tőke

Research output: Contribution to journalArticle

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Abstract

New 2-phosphabicyclo[2.2.2]octene 2-oxides (2 and 3) were synthesized by the Diels-Alder reaction of 1,2-dihydrophosphinine oxides (1) and dienophiles, such as N-phenyl maleimide and maleic anhydride. The X-ray structure of one of the products (2Ab) suggests that the phosphabicyclooctenes have a less strained framework than the phosphabicyclooctadienes described earlier. As a consequence of this, also confirmed by thermal examinations and semiempirical calculations, thermal fragmentation of the phosphabicyclooctenes requires more forcing conditions, than that of the bicyclooctadienes. The methylenephosphine oxide (10) ejected could be utilized in the phosphorylation of hydroquinone in moderate yield. Mass spectral fragmentation of cycloadducts 2 and 3 under electron-impact conditions seems to be in agreement with the preparative experiences.

Original languageEnglish
Pages (from-to)182-189
Number of pages8
JournalJournal of Organometallic Chemistry
Volume579
Issue number1-2
Publication statusPublished - May 5 1999

Fingerprint

Oxides
fragmentation
oxides
Hot Temperature
Maleic Anhydrides
Diels-Alder reactions
phosphorylation
Phosphorylation
Cycloaddition Reaction
Maleic anhydride
anhydrides
electron impact
examination
X-Rays
Electrons
X rays
products
x rays
maleimide
hydroquinone

Keywords

  • 2-Phosphabicyclo[2.2.2]octene 2-oxide
  • Energy profile
  • Phosphorylation
  • Thermostability

ASJC Scopus subject areas

  • Biochemistry
  • Inorganic Chemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Materials Chemistry

Cite this

The ability of 2-phosphabicyclo[2.2.2]oct-5-ene 2-oxides to undergo fragmentation of the bridging P-moiety. / Keglevich, G.; Steinhauser, Kinga; Keseru, György Miklós; Böcskei, Zsolt; Újszászy, K.; Marosi, G.; Ravadits, Imre; Tőke, L.

In: Journal of Organometallic Chemistry, Vol. 579, No. 1-2, 05.05.1999, p. 182-189.

Research output: Contribution to journalArticle

Keglevich, G. ; Steinhauser, Kinga ; Keseru, György Miklós ; Böcskei, Zsolt ; Újszászy, K. ; Marosi, G. ; Ravadits, Imre ; Tőke, L. / The ability of 2-phosphabicyclo[2.2.2]oct-5-ene 2-oxides to undergo fragmentation of the bridging P-moiety. In: Journal of Organometallic Chemistry. 1999 ; Vol. 579, No. 1-2. pp. 182-189.
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AU - Keseru, György Miklós

AU - Böcskei, Zsolt

AU - Újszászy, K.

AU - Marosi, G.

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AB - New 2-phosphabicyclo[2.2.2]octene 2-oxides (2 and 3) were synthesized by the Diels-Alder reaction of 1,2-dihydrophosphinine oxides (1) and dienophiles, such as N-phenyl maleimide and maleic anhydride. The X-ray structure of one of the products (2Ab) suggests that the phosphabicyclooctenes have a less strained framework than the phosphabicyclooctadienes described earlier. As a consequence of this, also confirmed by thermal examinations and semiempirical calculations, thermal fragmentation of the phosphabicyclooctenes requires more forcing conditions, than that of the bicyclooctadienes. The methylenephosphine oxide (10) ejected could be utilized in the phosphorylation of hydroquinone in moderate yield. Mass spectral fragmentation of cycloadducts 2 and 3 under electron-impact conditions seems to be in agreement with the preparative experiences.

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